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For sale by owner
  • $999,000

    21650 Overseas Hwy Unit 101, Cudjoe Key, FL 33042

    2beds
    1,200sqft
    : 
    $6,462/mo
    Get pre-qualified
    SingleFamily
    Built in 2007
    967 Square Feet Lot
    $-- Zestimate®
    $833/sqft
    $500/mo HOA

    What's special

    Dock slip includedShared heated poolFully furnished and turnkeyPrivate waterfront getaway
    Florida Keys Investment & Vacation Retreat Opportunity 21650 Overseas Highway, house# 101 – Cudjoe Key, FL 33042 Experience the very best of the Lower Keys with this rare opportunity to own a property that perfectly blends personal enjoyment with exceptional income potential. Whether you’ve been searching for a private waterfront getaway, a vacation retreat, or a proven income-producing investment, this property delivers on all fronts. Owned and successfully operated as a short-term rental since 2019, this home has consistently generated +\- $100,000 annually in short-term rental income, offering a turnkey opportunity for investors or buyers seeking a property that can help pay for itself while enjoying the Florida Keys lifestyle. One of the most valuable features of this property is the fully transferable transient rental license. Unlike many properties throughout the Lower Keys that face strict rental limitations, this license allows the home to operate similarly to a hotel with no minimum night restrictions — an extremely rare and highly desirable advantage in the Florida Keys market. Each home includes its own dock slip, perfect for keeping your boat, jet skis, kayaks, and other water toys just steps away. The community consists of only 11 homes, creating an extremely private and relaxed atmosphere. Owners and guests also enjoy access to a shared heated pool and the benefits of a very low, owner-operated HOA. The property is being offered fully furnished and completely turnkey, including established rental history and everything needed to continue operating immediately from day one. Enjoy boating, fishing, diving, and everything the Lower Keys lifestyle has to offer from this ideally located property in Cudjoe Key. Property Highlights Proven short-term rental income producing property $100,000 in consistent annual STR revenue Fully transferable transient rental license No minimum night rental restrictions Operated successfully since 2019 Dock slip included Exclusive 11-home community Shared heated pool Very low owner-operated HOA Fully furnished and turnkey Established rental history Ideal as both a personal vacation retreat and investment property Located in the heart of the Lower Florida Keys Asking Price $999,000
    58 days
    |
    293
    |
    8
    |
    Listed by:

    Property Owner (305) 316-4808

    This property is for sale by owner and Zillow, Inc. is displaying it at the owner's request. It is not subject to a listing agreement with Zillow, Inc. or its affiliates.

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 3
      • Full bathrooms: 3
      Heating
      • None, Other
      Cooling
      • Central
      Features
      • Flooring: Other
      • Has fireplace: No
      Interior area
      • Total interior livable area: 1,200 sqft

      Property

      Parking
      • Total spaces: 2
      Features
      • Exterior features: Other
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      Lot
      • Size: 967 Square Feet
      Details
      • Parcel number: 00174820000101

      Construction

      Type & style
      • Home type: SingleFamily
      Materials
      • Wood
      • Foundation: Piling
      • Roof: Other
      Condition
      • New construction: No
      • Year built: 2007

      Community & HOA

      HOA
      • Has HOA: Yes
      • HOA fee: $500 monthly
      Location
      • Region: Cudjoe Key

      Financial & listing details

      • Price per square foot: $833/sqft
      • Tax assessed value: $602,139
      • Annual tax amount: $5,854
      • Date on market: 5/30/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $5,313/mo

        Price history

        DateEventPrice
        5/30/2026Listed for sale$999,000+168%$833/sqft
        Source: Owner Report a problem
        12/20/2018Sold$372,750-17.2%$311/sqft
        Source: FLKMLS #583015 Report a problem
        11/30/2018Listed for sale$450,000$375/sqft
        Source: Truman Annex Real Estate Co., Inc (Dba Compass Realty) #P112084 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,854 +13%$561,839 +10%
        2024$5,180 +7.5%$510,763 +10%
        2023$4,817 +7.5%$464,330 +10%
        2022$4,482 +6.3%$422,118 +10%
        2021$4,216 +5.4%$383,744 +7.5%
        2020$4,000 $356,943 +3.3%
        2019$4,000 +2.4%$345,684 +3.5%
        2018$3,906 +2.1%$334,022 +2.6%
        2017$3,825 +6.7%$325,471 +6.1%
        2016$3,583 +4.2%$306,628 +25.7%
        2015$3,439 $243,916
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 33042

        Getting around

        18 / 100
        Car-Dependent
        59 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Monroe County
        • Middle: Monroe County
        • High: Monroe County

        Source: The MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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